Synthesis of conformationally restricted sulfonamides via radical cyclisation

Tetrahedron Letters

Volumn 51, Issue 20, 2010, Pages 2681-2684

  Biswas, D ^a   Samp, L ^a   Ganguly, A K ^a  

^a Stevens Institute of Technology   (United States)

Author keywords

Heterocyclic chemistry; Radical reactions

Indexed keywords

SULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; PHARMACOPHORE; RADICAL CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77950595961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.089     Document Type: Article

References (9)

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3. Rabaseeda T., and Hopkins S.J. Drugs Today 30 (1994) 557
4. Debus O.M., and Kurlemann G. Epilepsia 45 (2004) 103
5. Katritzky A.R., Rachwal J.W.S., Rachwal B., Macomber D.W., and Smith T.P. Org. Prep. Proc. Int. 24 (1992) 463-467 The reviewer pointed out this reference to us
6. Mata M.L.E.N.d., Motherwell W.B., and Ujjainwala F. Tetrahedron Lett. 23 (1997) 137-140
7. 4, filtered, concentrated and purified by silica gel column chromatography to obtain compounds 13 (0.41 g, 73.7%) and 16 (0.069 g, 12%).
8. Yields are indicated in parentheses; however, they were not optimised. Compounds were crystallised from a mixture of dichloromethane and hexane. Melting points of the crystalline compounds are shown below: 12 (53-54 °C), 13 (57-58 °C), 14 (100-102 °C), 15 (75-77 °C), 16 (68-70 °C), 20 (81-83 °C), 26 (125-126 °C), 27 (169-171 °C), 35 (106-108 °C), 36 (143-144 °C), 37 (98-100 °C).
9. NMR and high resolution mass spectra of all the compounds described in this Letter were consistent with the assigned structures. Assignments were further confirmed using 2D NMR experiments.